0

"
Now I8 Part ul = fi 11 未去 !

Addition Reactions of carbony 1 Compounds

NucleopbiliE .

即然講得係 Nnt Addition , ⾃然要睇 Nw 點同 carbony 1 react

=3 reaation 通常會⽤ acid as catalyst ( or LewTs acid )

0
…
≈ 0 _
H OH

3119
π
+

只 H
+ …
~

protomated car bonyl

group

Carbomy (
Compound & reacitivity :

① Aidenyde ② Ketone ③ estev

_
都係因為 share 者
0
0 0
charge
" > > “
"
^ -
1

-⼂
R R1 R OR
k H

Nn
θ
都帶 ve charge = 可以 attact of carbon

① H ROC
② ⑤ CNO

其他有 chaoge 就要 activ nteo 左 Oatom 先

e .
g .
alconoladditiou

H 2 OR ⑥ O - H
0
⼀ ⇌
" ⼋
"
⼀ R OH

∞
e N
9 ,
…

“
0 - H
0
" “
, ,
NH R
—
2

θ
 0
"

① Hydvide ( H 1

H 來源 : ① GA 1 H 4 ( LAH ) ② NGBH 4

solvent ROH
bawn
s t
strong
- e
.

can ase
protic e -

9 .

solvent = EtrO / omly reduce cot and COR

THI
.
-

好啦睇到呢度都知就係中學所學既 reduction

⾸先係 aldqnnde 同 Ketone :

ConditTons :
① H - ②H 2 O

Products oH
= _

☆ 00 ≈ A OH
⑪ 11 H H OH H2 O 1
1
-

+ OH

f
~ , ,

⼝ ⼈
…
… 以 k w
。
H

如果係 estev :

仲記得 ester → aord talconol ?

所⼈就當 acid 都 weduce → 10 alcomol

同埋先分開變做 aldenyde + alcomol 再 reduce

⑪ H , "
0

+ RO
θ

MoRn 7 7
负 oRil ~

θ
纪 H
o
H
AiH 4

, R
^
oH
 0
"

② OrTgmard Reagent
EtrO
R
preparatTon R X t
Mg > MGX
-

:
-

=
7 grigmard reagent 既⾓⾊同 RO 差唔多 s 0 lvent =
Et 2 O

( dieth nl etnev
)
= 7 is a
good Nut aond base

^ ^
H 3 C 0 CH 3

For A ( dehandeand ketones :

0
→ 0

合⼼
10 10 alconol
0

→ r alconol → 30 alcohol
在 H
R
/
k
( formaldenyde )

因為 NnO ⾃⼰係⼀ R 1 所以 product ⾃⼰升⼀度 alconol :

3

N④
100
≈
^0 H oHz
_

OH
_

tt≈
0
~ , , tmo
⼼
;
+

'
Omaxtno
⼝ ② H 30 品

For esters 30 alconol

因為⾸先 ketone 再 redace 30 alconol

-

reduce ⼯次 + R → →

可
”

9 10 0
,
⼋ ow
0
4 >
☆ R
" + OR

σ“
0
⼝

sn
"
k
omgx
*
 0
"
③ Alconol

+
Catalyst =
H ( acTd )

⽬標係將 Carbonyl group → -

OR + -

OH → 2
-

OR

但就唔係 aftact centve ⼒加⽊ “ 先 ,

係打入 Oatom 先 , 再打 Catom

+ 莊⼀⼝
“

⾸先 R OH
" 00 “ 0 R

,
µδ ⼗

然後再 react
bk "

⺿
O atom

I ↑
% 0

”
- H

“
0k
"

+ R -

OH
~ ,
∞

↑
2 R

Aftact
"
OH

Catom
→

R
60
" ⼀

otH
再帶走 ↑
“

1
Hx ↓

- 20
R OH +
"

^
"
”

⿒
→
OR
-

(
2 times

⑪
再整
“
I
_
OR

gromp

上⾯個 _
OH

變 H 2 O 走
+ 0 H

※ OHT
2

"
R

-e
i o
÷
—
∴^
“
OR
 0
"

all step reveusible

:
如果 excess H umuydrons ) → suitt 右
→
如果多⽔ + H+ shift 返左 Chydrolysis 了

Acttals 同 Katals 其實有保護其他 functonal group 既作⽤

例如 :

reductionX 7
⼋
哈
Brmg W

~^
0
1 . ~~≥
因為 :

① stabikratTonOatom
,
會拉 e 過去 ,
令 R 比唔夠 negatior
② molecule ⾃⼰會有強烈 partTal cnauge = 7 Intermoleonlal fovce

所以如果想做 reaction , 要⽤ HO Λ _
OH
andH
+
保護也先
ecg .

OH
product
Br 1
…

… … 9

“
。 ∵
^

+
OH H
OH
~ lag )
Hf

iugBv
V

BU

σ
1
0 0

react 完
ttzO
0
“
~
Mg
} BrMg

0 0
 0
"

④ Primary Amimes / HydvarTmes

oaminesl N
-

(⽇ ) R
“
RH > “ ( iumines )
-

H
⼼
AuH
n
-

[B ) Ar -

N NH ,
{ nydrazone 了
-

2
"

LhydrarTne )

mv
OH

i
⼗
= ⼀

H OH
O
" " \

! hkH
^

“
. " 以

世 、

HtoHze
-

世
“

0
NR -

H
、

.
"

此
⼀

N
+ H 2 O
“
⼀

NR
"

同 alcouol addition ⼀樣係reversible :

excess umime =
) shift 右
+
HrO + H shift 在

⑤ HCN
Δ DH
…
00 GN
H
o → 「
-

Sl
119
0 w
(

\
\

… CN
CN

: CN

wutaaidICN
weak . a
⼆
⽤ NaCN / KCN + H 2 SU 4 比較好

100
…
世 OH
O Na
NaCU HrSO 4 ↑
" 7 >
1

CN CN